1. NMR Chapter 13 1 H-NMR Spectroscopy CHEMISTRY 220 Spring 2003

2. MEK (2-butanone) a b c Signal b expanded Signal c expanded Integration: ____mm #protons a - 58  3 b - 40  2 c - 59  3 Splitting: ____Multiplet “sees” a - singlet  0 H’s b - quartet  3 H’s c - triplet  2 H’s

3. Coupling Trees for MEK

4. Butanal Integration: ____mm #protons a - 33  1 b - 65  2 c - 98  3 Splitting: ____Multiplet “sees” a - singlet  0 H’s b - d of q  3 H’s c - triplet  2 H’s a b c Signal b expanded Signal c expanded

5. Coupling Trees for Butanal

6. 1,3-Dibromopropane 4 2 a b a Plane of symmetry b b (quintet) a (triplet) identical

7. Isopropyl butanoate a b c d e Integral a – 3p b – 6p c – 2p d – 2p e – 1p a b c e d e (septet) d (t) c (sextet) b (d) a (t)

8. p-Methylbenzoic acid Effect of an electron withdrawing group a b c d Deshielded by resonance

9. 1-Methoxy-4-methylbenzene Effect of an electron donating group a b cd Shielded by resonance

10. Deuterated Solvents Deuterium ( 2 H) has a spin quantum No. of 1. Deuterium does not couple to protons ( 1 H). Different deuterated solvents can affect chemical shifts.